Japanese works tend to play up a few common traits for this character type: a combination of a gaudy outfit, a Noblewoman's Laugh and absolute narcissism. He also often has a crush on the Big Bad, The Dragon, or in more humorous works, the Chaste Hero.

Examples:

Yuda represents the essence of this trope, particularly as played in anime. Outrageous outfit? Check. Annoying laugh? Check. Insanely self-absorbed and narcissistic? To eleven. Also obviously, albeit not explicitly, a Depraved Bisexual.

Dekai Babaa is a giant thug disguised as an old woman and tried to give poisoned water to the heroes, but his old lady facade wasn't convincing enough for them.

In Akazukin Cha Cha, Doris is the twin brother of Dorothy who is in love with their childhood friend Seravy, who has Belligerent Sexual Tension with Dorothy, ever since she had a makeover which Seravy hates (she changed her natural golden curls to a straight red-pink hair). In an effort to win Seravy's affections, he himself had a makeover to look exactly like his sister's original appearance. Naturally, this only Squicks Seravy out to the point he is usually very violent to Doris (and only to Doris.)

Haou Airen: Huo Long. His heart is in the right place, but he is a Triad member.

Mr. 2 Bon Clay of Baroque Works, the only Baroque Works officer without a female partner, since he counts as both the man and the woman. His alias reflects this, being a combination of a number (traditional for male officers) and and a reference to a holiday (traditional for female officers). Though after losing, he pulls a Heel–Face Turn, like many One Piece villains, transforming into a Wholesome Crossdresser.

Taken to absurd levels with Emporio Ivankov, the "queen" of Kamabakka Kingdom. His design was modeled on no less than Dr. Frank N. Furter himself. When he was arrested and locked in Impel Down, he founded a Prisoner's Paradise between the prison's two harshest floors where everyone dressed in fishnet stockings and switched freely between genders thanks to Iva's hormone controlling "Horu-Horu" Fruit.

And yet despite his absurd level of creepiness, he can still be considered one of the top good guys of the entire One Piece world, being a commander of the World Revolution Army, just about the only faction who opposes the corrupt World Government for presumably altruistic reasons (for most pirate crews it's more a case of Evil Versus Evil)

Kamatari of Rurouni Kenshin, though he's portrayed fairly sympathetically and is driven by an unrequited love for Shishio. Otowa, on the other hand, is just a Psycho for Hire.

Jakotsu from InuYasha has a crush on Inuyasha (and flirts with Miroku and Sesshomaru), but later is shown in a more sympathetic way through his genuine friendship with Bankotsu. Supposedly, Jakotsu was originally supposed to be a woman, but the author changed it because she didn't like the idea of the characters killing a human woman, undead or not. Regardless of the gender-switch, Jakotsu is also the most psychotic and murderous of the Band of Seven, with quirks that include sadism and a tendency to torture his "lovers" to death. For example, he says Inuyasha's ears are so cute he wants to cut them off.

The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine. This only applies in the 2003 anime, however, as Envy in the manga has no gender (or, according to Word of God, no one knows Envy's true gender – not even Envy). So whether or not they have one is up for debate. If they do, they're as lost as we are.

The serial killer Barry the Chopper first appeared dressing as a woman when out delivering meat from his butcher shop. He kidnapped Winry and almost murdered both her and Edward.

Fish Eye from Sailor Moon has shades of this, though is clearly intended to appeal to the fetish. As the other villains disguise themselves, the Hand Wave is dressing as a woman is simply a modus operandi to cover the left over type of victims - males - as Hawks Eye targeted older women and Tigers Eye targeted younger women. He actually dresses as a male for a specific mission (targeting a gay fashion designer), and while exclusively using male pronouns when in circus attire, will only use feminine pronouns when disguised. Ironically, his femininity seems to make him closer to Earth, and he has the first Heel–Face Turn of the season.

Also Zoisite, though played a bit straighter (no pun intended) than the openly camp Fish Eye. Guilty of feminine appearance, romantic relationship with a male, shrill laugh, and sakura petals everywhere. Fits this trope because he actually crossdresses as the title heroine in order to lure Tuxedo Mask out of hiding. Though the crossdressing was Kunzite's idea, not his.

Zoisite and Nephrite both crossdress to disguise themselves in the manga. Also, it is not Fish Eye but Hawks Eye who crossdresses in the manga.

Also of note in regards to Fish Eye, in one episode he dresses up as a female ballerina with clearly visible breasts and cleavage. Regardless if it was magic or not, he showed he was really committed to pulling off a good disguise.

Elendira the Crimson Nail from Trigun Maximum (the later volumes of the manga), although he or she is most likely a transsexual woman.

Given the body-mod capabilities of Gunsmoke science demonstrated in the series, she could be, but could also still be male. Either way, she's scary as hell, one-upped Legato by some way, but was sadly too freaky (as much for the 'fighting style based on graphic impalement with giant red hardware from nowhere' bit as for the transexuality) to get into the anime.

Notable for the fact that, unlike Kamatari above, although she's competing for the affection of a man who will never look at her she's easily the most sane and the most physically powerful force he can mobilize, until he goes Million Winged Angel. (Meanwhile Legato's 'eat steak with no hands' and 'float around in sarcophagus of doom' lines have inspired mutinies out of sheer embarrassment from his subordinatees.

Incredibly drawn-out death sequence was solid horror. Can we get Freudian about those humongous nails ramming through bodies, please?

The Big Cheese from Samurai Pizza Cats. Strangely, his flirting with male subordinates was mostly left intact.

Orochimaru of Naruto, who is actually a man in a woman's body (at the start of the series) Shapeshifting as an effeminate male. Just to make matters creepier, he first shows up wearing a woman's face as a disguise, after tearing it off.

Flame of Recca's Kurenai may be effeminate, but the real version of the trope doesn't appear until very late in the manga when the clone Aoi poses as a female student. Recca seems nonplussed considering the much stranger people he's met at this point, except in being completely confused by the reformed Aoi trying to explain his complicated backstory.

Monster offers a particularly creepy example in which this trope is not played for laughs. Johan impersonates his twin sister, Anna, in a flawless fashion that is quite disturbing. He still manages to sound threatening while wearing a dress, which says a lot about how ultimately creepy he can be. Interestingly, the creep factor doesn't come so much from the gender implications so much as how much it represents his concept of himself and Anna as the same person.

Charlotte Chuhlourne is a flamboyant Magical Girl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his pelvic area. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his resureccion, called Reina des Roses, he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a rose in mind. He's extremely proud of his muscular strength and his costumes are designed to show off his body as much as possible.

Giselle is accused of being a man by Yumichika but neither confirms nor denies the accusation. While she actually dresses in a quite wholesome-looking fashion, the more that's revealed about her, the less wholesome she appears. Yumichika claims she reeks of semen, and a resurrected Charlotte also identifies her as "resembling" him after sniffing her. Giselle creates zombies by infecting shinigami with her blood and even kills her quincy friend Bambietta to turn her into a zombie. She drools when excited and the thought of using her blood on others seems to turn her on.

Team Rocket, most of the time: In Kanto and Johto, Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode, where James has a pair of inflatable breasts that led to the episode being banned. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.

Harley is also a great, albeit much less permanent, example, but technically he only crossdresses once.

Lelouch does this at least twice in the picture dramas. In one of them, the Student Council has a crossdressing festival so everyone crossdresses (and Suzaku... mentions having done it a few times before?).

Tsubasa Kurenai from Ranma ˝. A straight guy who dresses up like a schoolgirl and relentlessly stalks former schoolmate Ukyo Kuonji (a straight girl who spent most of her life dressing up like a guy) while disguised as various inanimate objects. Tsubasa is assumed to be a lesbian at first because he's very passable and is only interested in women. Ranma tries dating Tsubasa while in male form to set "her" straight, only to find that Tsubasa is a boy.

Mariya from Maria†Holic does a very convincing job as a girl. Since this is an all girls' school, no surprise that he gets Kanako falling for him the moment they meet. He's also incredibly sadistic.

One early example of this trope would be Rock, from the various manga by Osamu Tezuka. Who, in his more villainous incarnations, would often disguise himself as a woman.

Yuuji Fukunaga from Liar Game starts off as this, but slowly pulls a Heel–Face Turn and becomes one of the main supporting characters while still making a better looking girl than most of the female cast combined.

The Kirbyanime has Escargon, a Camp Gay villain with a not-so-subtle crush on his boss who has crossdressed a few times (usually because said boss wanted him to).

Fumiya Ninomiya from Wandering Son crossdresses just to impress Saori Chiba. While not an outright "villain", he is portrayed as a bit of a slimeball when compared to the actual transsexuals.

Sakurako from Sakura Gariis actually Souma's brother, named Youya. He stole his mother's name and dressed in her clothing after she died, having been traumatised after witnessing said mom's murder at the hands of Souma and Katsuragi. Soon after his gender was discovered by Masataka, he tried to kill both him and Souma, then had a heartbreaking Villainous Breakdown and committed suicide.

Black Butler: In episode five of the second season, AloisTrancy dresses up as a maid to lure Ciel into his bedroom so he can flirt with him and take his eyepatch. It's also shown that he has a few dresses in his wardrobe.

In My Bride Is a Mermaid, Both Sun and Lunar's fathers try to get to know their daughters a little better by exploring some research into teenage life (I.E: they explored a goofy Dating Sim). The end result completely horrifies EVERYONE else, especially the two girls. Seeing the anime equivalent of the Terminator wearing a sailor fuku is not a pretty sight. Funny, but not pretty.

Baikinman from Anpanman will commonly disguise himself as characters to either get the character he's disguised at in trouble, or to get free food out of people. Most of the time, he'll end up disguising himself as some of the female characters...even if Dokinchan is with him. When he disguises as a female character, Dokinchan will either crossdress as a male character that works with the female character, or even sometimes make up a male counterpart to the existing female character.

anohana: The Flower We Saw That Day: A more tragic example. After the death of his childhood love, Menma, Yukiatsu takes to dressing up as her and running around their childhood hangout at night. This is his way of coping with his loss.

Happens, accidently, to Sora in Kingdom Hearts II, when the fairies put him in a ball gown (complete with tiara) while designing a new outfit for him. It's clear from that scene that he hates cross-dressing.

Kaito from Himegoto - Juukyuusai No Seifuku comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a Jerk Ass who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipilative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely Transsexual than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.

Osamu from Bokura no Hentai has shades of this. He's portrayed as less emotionally stable than the other crossdressers.

Izumi from Boku to Boku isn't too villainous but he's portrayed as a perverted, more mean spirited foil to the Wholesome Crossdresser Jun.

In Kara no Kyoukai Lio Shirazumi starts dressing and styling himself like Shiki and committing murders like this. The fact that he manages to look seriously creepy in a rather silly looking skirt says a lot.

Comic Books

The Purple Marauder, transvestite women-hating archnemesis of the Anti-Hero Lusiphur, the elvish protagonist of the series Poison Elves (originally titled "I, Lusiphur") by late artist/writer Drew Hayes (1969-2007). The Purple Marauder (a human) is a foppish Zorro-like vigilante swordsman who terrorizes the world of Amrahly'nn with his rapier and mustache-twirling villainy but mainly with the sight of his hairy fishnet-clad legs. He dresses, as the name insinuates, all in purple from head to toe: large purple hat, purple women's dress, purple boots. His sworn mission: To convert men from the ways of lust and women.

While he's technically more of a mercenary with a small modicum of heart and it was only the once, when Deadpool spent a brief time with the X-men he insisted on wearing one of their costumes. Specifically, Marvel Girl's. For unknown reasons he also retained the underwear from the costume underneath his suit even when he went back to his black-and-red tights.

In American Flagg!, Ivor Overholt, who makes himself into a doppelganger for the presumed-dead Peg Krieger in order to seduce and blackmail a character who was obsessed with her. Possibly a borderline example of Easy Sex Change as well, though the character still had his original genitalia and still appeared as a man in public.

Golden AgeWonder Woman foe Blue Snowman was a rare female version of this, being a woman who dressed up in a male snowman outfit to commit crimes.

Pretty much everybody else (yes, even the dolphin) is just as grossed out when Ace reveals it, in fact.

In Beyond the Valley of the Dolls, the character Ronnie 'Z-Man' Barzell goes on a murderous, drug-induced rampage dressed as "Superwoman". Then again it's unclear if Z-Man really is this trope or is actually trans, considering this scene followed Z-Man revealing female breasts to Lance.

Even James Bond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaption of Diamonds Are Forever. Also, Thunderball has an old enemy of Bond disguised as his own "widow".

In The Dark Knight, The Joker disguises himself as a nurse in one scene to get to Harvey in the hospital. Instead of wearing unisex scrubs or just dressing as a male nurse, he goes drag, complete with a wig. It manages to be funny and creepy at the same time. It was likewise intentionally invoked, seeing as he'd kept his Joker facepaint and green hair color (and displayed in an earlier scene that he was willing to go without them when making a sincere effort to disguise himself).

Freebie and the Bean, a buddy cop film from the 70's, features a beautiful blond crossdressing antagonist played by Christopher Morley.

In Death Wish V: The Face of Death one of the villains is Fredrick "Freddie Flakes" Garrity (not at all played by Sid the coroner fromCSI: NY), a high-priced mob assassin (nicknamed because of his frequent dandruff) who not only crossdresses during one of his schemes, but later, when hanging out with his girlfriend, comments her shoes, saying he can't wait to see how they fit. (He also has what is quite possibly the stupidest death of the series, immolated by an exploding soccer ball).

"Despite his stupid name, I have to admit that Dark can be a pretty interesting character. Until this point in the movie we never actually see him. When he walks onscreen, however, he steals the show, mostly because he is wearing women's clothing. Without explanation. When you see a cross-dressing serial killer in a movie, he is usually wearing makeup in a dress. Something that says "hey, I am a psycho and I wear clothes that obviously belong to a woman." This is not the case with Dark. Instead of a skirt or something, he wears a pink tube-top and woman's executive jacket with padded shoulders. And, again, this is never explained. It is almost as if the movie goes out of its way to ignore this fact, like the only person who would take the role was some cross-dresser at the bus stop and they're trying to downplay the fact."

Marion Penrose in Unhinged, due to his mother being an insane misandrist.

The villain of the Hong Kong slasher film He Lives By Night is a crossdressing serial killer who prowls the streets at night, brutalizing women before strangling them with white stockings.

Harry Russo from Schizophreniac: The Whore Mangler and its sequels, apparently the result of his horribly abusive parents wanting a girl.

While committing murders, Leonard Marliston from Cherry Falls dresses like his mother.

In Shine, David (it's implied) sleeps with one while he is studying in the Royal College of Music.

In Filth, the main character is this, although, frankly, he's creepy independently of this habit and the actual crossdressing is played for sympathy.

Played distressingly straight in the otherwise comic 60s caper flick Caprice, in which it’s revealed that villainous Stuart Clancy got into the fashion industry so he could wear women’s clothes.

The Toxic Avenger: One of the two thugs in Cigar Face's street gang is a cross dresser in a dress, wig and make-up. While the Toxic Avenger is ripping his buddies apart, the cross dresser stands aside to reapply his make-up before joining the fray.

The Borrower: Scully escapes from the hospital by assaulting and knocking out the female cop who was guarding him. He ties her up and rapes her before he steals her clothes to walk out of the hospital. He even puts on her underwear and lipstick.

Norman doesn't really fit the stereotype given in the trope description— his cross-dressing is to give his other personality a more convincing appearance.

In the Redwall series, Emperor Ublaz Mad Eyes is a possibly-not-intentional-on-the-author's-part borderline example. The silk robes, painted nails and perfume he is mentioned as having in his first appearance are par for the course for an evil exotic emperor, but the entire book revolves around him attempting to steal a famous set of six large pink pearls to put in his crown. He goes so far as to slaughter entire tribes to get the things. He also stops in the middle of his angry Mirror Monologue to debate what he's going to wear for the victory parade; "If I had the Tears of all Oceans now, they would be set in my crown, all six of them, wondrous rose-colored pearls! I would don my green silk mantle, or maybe the black one with gold trim ..."

An odd little novel called Pest Control by Bill Fitzhugh featured, among other things, a diminutive hitman who likes to dress up as a little girl to do his hits. He also bangs a repressed middle-aged mom who has a thing for midgets and circus peanuts.

Antiheroic example in Discworld's Nobby, who picked up the habit in Foreignland and has gotten to the point where he asks:

Nobby: Do I look good in taffeta?

Angua: Erm, yes. Lovely.

Nobby: Really? You don't think it makes me look too fat?

Herman Goering was depicted as a transvestite in A.E. Hotchner's novel The Man Who Lived at the Ritz.

Bèbelle from Malevil. Part of it is being creepy and evil, another part is using Disguised in Drag to infiltrate settlements prior to his marauding army invading.

I, Claudius features a scene where Caligula (see below under real life) summons the title character and two other men out to his palace unexpectedly, scaring all three shitless because they expect to be executed, only to shock them when he prances out in full drag and does a performance for them. Also mentions the real life incidents where he dressed as Venus.

Live-Action TV

Borderline-ish example: the second season of Skins features a character who, while still visibly female, binds her chest and dresses in boyish clothes with hopes of making herself more attractive to the object of her romantic obsession, who happens to be gay. It doesn't work.

Alonzo Torquemada of HBO's OZ is a tall, strapping Hispanic crossdresser with one glass eye and a penchant for hallucinogens. While not quite as evil as his namesake, Torquemada isn't above slipping his enemies poisoned dope, or seducing Miguel Alvarez.

When Luke and Laura on General Hospital went on the run in 1980, they eventually encountered Sally, a hitman who wore a dress.

The episode "Machismo" of Criminal Minds was Ripped from the Headlines about Mataviejitas, "The Old Lady Killer." It featured a man who dressed as a woman to gain entrance into old elderly women's apartments to kill them. The actual case is a subversion. Authorities believed the killer was a man dressing as a woman; in fact, she was just a woman. It's worth pointing out that the show lampshades and (perhaps?) subverts the trope, explicitly stating that their villain is not a crossdresser: dressing as a woman is not a lifestyle for him, but a tactic.

It may have actually been more than a tactic. Before he became a serial killer, he was a serial rapist, and even then he wore dresses and the like, despite having no apparent reason to (he didn't use a ruse then, just blitzed the victims, who never really saw him, since he came up from behind and blindfolded them).

The UnSub in "Limelight" is a crossdresser, wearing his victim's clothes as a means of reliving his murders.

"Conflicted" takes the cake of this trope, with an UnSub who is a cross-dressing serial killer alter personality who lures and disarms her victims sexually and then rapes them (penetratively). The cross-dressing is more convincing to the characters than to the audience, and to top it off, the UnSub has a habit of suddenly cross-acting without redressing.

While The Master spends the majority of the Doctor Who story The End of Time wearing a black hoodie, the climatic sequence where The Master uses the immortality gate to transform nearly the entire global population into copies of himself, sees him don a variety of outfits. The sight of John Simm in a dress applauding himself while giggling insanely can also be counted as a Crowning Moment of Funny.

Real Life head of the Nazi Luftwaffe Herman Goering was depicted as a transvestite in a 1988 TV Movie, The Man Who Lived at the Ritz, based on A.E. Hotchner's novel.

In the season five episode "Demons and Angels", Lister is running for his life from the evil versions of the Red Dwarf crew, until he runs into Evil Rimmer ... wearing what is best described as a Dominatrix-type get up.

In another Series 5 episode, "Quarantine". When Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding MrFlibbles. Also lampshaded:

[Rimmer appears in an observation window. He is NOT in uniform.]

Rimmer: Is something amiss?

Lister: [trying to disguise the tremor in his voice] Amiss? God no. What could possibly be amiss?

Community Dean Pelton could be considered a Wholesome Crossdresser, as he's not a bad guy; but in-universe, most people are weirded out by his bizarre (often revealing) outfits, which puts him in the territory of this trope. It doesn't help that he's also a dalmatian furry fetishist with a serious crush on one of his students. The students note a few times that he'd be less creepy if he would just admit he's a crossdresser, instead of constantly pretending to be forced to borrow clothes from his nonexistent sister.

JAG: In "Retrial", a sailor had unbeknownst to him hired a transsexual prostitute. When finding out, the sailor changed his mind and the prostitute threatens him with a knife.

In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It doesn't evenmake sense in context.

Barry Zuckerkorn goes to the City of Industry to pick up a prostitute, but quickly drives off when the prostitute reveals that she is not a man in drag. There are also some hints that Barry himself is a closet cross dresser.

While he was hiding in the attic, George Sr. dresses in his late daughter-in-law's maternity clothes. During a hug, Michael also notes that he was wearing her perfume, too.

Guiding Light. Brent Lawrence, after drugging and raping Lucy, faked his death, then returned to town as Marion Crane, in order to befriend and ultimately terrorize his unsuspecting victim.

In the NYPD Blue episode "Andy Appleseed" (season 11), the detectives go to the apartment of a murdered woman because they think the suspected murderer may be there. They find him in her closet, trying on her bras and panties.

Mr. Robot: An apparent bigwig in the Dark Army, a mysterious hacker mercenary organization, is dressed as a woman during his brief meeting with the hero. It's never commented on, and in a later scene he wears a classic men's tuxedo, possibly implying that he was deliberately using the trope to mess with the hero's head.

White Rabbit Project: The Wardrobe Malfunction legend has this as one of the attempted escape shenanigans in the "Jailbreak" episode. A convict disguises himself as his visiting wife, trading places with her, to escape. The title comes into play in that the convict was poorly disguised, couldn't act like a woman convincingly, and got recaptured within 15 minutes.

Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in Dissidia: Final Fantasy. Then again, given that in the same game his official preferred weapons are flutes this might be an invocation of the Ruleof Funny.

Flea from Chrono Trigger. A popular fan theory that made it into some fanfic was Flea, being from a race of monsters, doesn't worry about the details of what humans wear so much as wear what he thinks is cute.

Another notable game example is the villain Alfred Ashford, from Resident Evil – Code: Veronica. He not only dresses in drag to pose as his own sister, but has an irritatingly mincing laugh and an extreme hatred towards the female protagonist, Claire.

Plus, he has an obsession for the Big Bad that could be taken as a crush, despite the fact that the Big Bad is his sister.

The SNK Gals FightersFighting Game has "Miss X", who is essentially the badass Iori Yagami in a sailor uniform and a bandit's mask. Predictably, no one in the rest of the all-female cast falls for it, and all of them point it out immediately.

Gao from Rhapsody: A Musical Adventure. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out of place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.

Ganbare Goemon is rife with these, the most prevalent being Sister Bismaru, Ebisumaru's descendant who dresses like a cross between a nun and a miko.

Justice from Guilty Gear counts, if only because of the huge crotch spike in her armor ...

There's also the tendency for people to identify mecha as male unless they look distinctly feminine. Even without the crotch spike, she looks sort-of gender-neutral, and thus would likely be identified as male at first glance.

More obviously, Testament in the first game, which also doubles as the game where his gender is the most ambiguous (thanks to him practicing his Voice of the Legion.) Later games make his gender more obvious and his change in allegiance make him more of a Wholesome Crossdresser.

Final Fantasy Tactics A2: The Night Dancer is a cross-dressing Camp GayBangaa. He even wears lipstick (on a Bangaa!) and eyeshadow and refers to himself as female, but fights with him tend to be fought under the "No harming the opposite sex" law, which outs him as male by the fact that female characters attacking him break the law while male characters attacking him do not. (On the other hand, some are so convinced by his insistent female identification that they really believe that he's a she and the law identification is a bug.) [1]

A man in Fable II is wearing a very crude attempt at a home-made woman's outfit. It turns out that he's insane and trying to feed people to his adopted family of goblin-like monsters. The game allows the player character to cross-dress, but no other characters do.

In Saints Row 2, Saints Row: The Third, and Saints Row IV the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a Transsexual through Easy Sex Change, if they so desire. This can go into "Creepy" territory instead of "Wholesome" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with wrestling moves and nut punches when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a Brute, an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by the Syndicate and it's funny.

The Medic in Team Fortress 2, sort of. He has an unlockable wig that's in a Geisha style with a comb and small flowers, leading to a Broken Base over those who thought Valve was pandering to the fans who wanted more Ho Yay (not all crossdressers are gay and not all gays crossdress, guys). If you know your history, geishas were originally all male. Regardless, it's a compliment. It's a Total War: Shogun 2-tie-in item, and geisha are some of the most badass units in that game.

Though Ghirahim from The Legend of Zelda: Skyward Sword has a pretty effeminately flamboyant appearance, he generally doesn't seem to be outright wearing women's attire, as would be true to this trope. Still, a few elements of his appearance seem to border on it, particularly in the way his face looks like it's covered in women's makeup, e.g. heavy pink eyeliner and white lipstick.

Yuga from A Link Between Worlds is an androgynous male antagonist who is obsessed with beauty and perfection.

beatmania IIDX 19 Lincle's Lincle Kingdom event features Rche, one of the bosses of the event, representing Pride. He is dressed very femininely and his gender is often (but not always!) censored in supplemental material. His name is a play on "Lucifer", and his "attack" consists of him suddenly transforming into a goat and firing at the Q-pro.

Plants vs. Zombies 2: It's About Time: In the Zombot Multi-Stage Masher fight, Dr Zomboss stands on a stage and changes his clothes to fit the current Jam. During the Pop Jam, he dresses up like a popstar girl with a dress and red wig. Take note that Zomboss is a diminutive male zombie with an oversized brain.

Undead Drag Queens appear as early-game enemies in Shin Megami Tensei: Devil Summoner: Soul Hackers. You could potentially recruit them, but given that they're of the Dark affinity and you only get the ability to recruit Dark demons quite a bit later in the game, it's not worth it except for 100% Completion. Recruiting one (or getting one through fusion) reveals in the Compendium that they are men who somehow became zombies as a result of their devotion to cross-dressing.

Dark Sun Gwyndolin from Dark Souls was a male moon god born to a family of sun gods. As the moon is associated with femininity he was raised as a daughter and wears feminine clothing which makes it looks like he has breasts. The 'creepy' part comes from the fact he lurks in a hidden tomb and has tentacles for legs.

Mettaton from Undertale is a complicated mess. Originally he is a ghost, which are supposed to be genderless, yet his house is "girlishy" pink. When in his casual robot form, he's always referred to as "he", but he performs his Villain Song in a dress. When in his EX form, he's still referred to as "he", but has some feminine characteristics to his design: most notably, slim legs that he adores. His body design also contains pink colour in great amounts (though that doesn't really matter, as most of the time we see that form, it's in battle mode, which is mostly black-and-white anyway).

Last Res0rt's Kurt Striaeta is not-so-ironically nicknamed "Geisha" and shown in his mugshot wearing a very feminine kimono. The surprising part is, he's actually one of the few "explicitly evil" criminals in the comic.

Nicholas in Samurai Princess has a very serious case of a bad man trying to be a woman. He has so far been shown in a geisha-like dress, a catsuit and, heaven forbid, a maid outfit.

Red Mage from 8-Bit Theater often wears a dress for not always apparent reasons.

A psychopathic but not overtly effeminate mook in a skirt appears near the end of Shadow Girls. Since he's also an obvious cyborg it's implied that what's under the skirt isn't exactly normal either.

A female example in Elsanna Bram Stokers Dracula, where Elsa crossdresses as a Victorian gentleman. As a result, Anna (as Mina Harker's expy) does not have a good first impression of her.

Web Original

In Survival of the Fittest v2, Damien Carter-Madison comes across women's clothing inside a wardrobe... and starts playing dress-up. One of the outfits he tries on is a sailor fuku, of all things. Note that he is a well-known villain of that version.

Douchey McNitpick is hinted to be one in "The Next Top 11 Fuck-Ups"; he's stated to have a corset amongst his wardrobe and apparently does this enough to know the difference between a Georgian dress and a Victorian dress.

A fan video for Mr. Bungle's Pink Cigarette revolves around a woman being stalked by a man in a dress and a wig with lipstick smeared all over his face. Adding to this is the fact that there's a recurring fantasy sequence where he's sweeping her off her feet rather than attacking her, and in those shots the same character is dressed in a suit without the makeup or wig.

In the Joe Oriolo Felix The Cat episode "Blubberino the Whale", The Professor briefly disguises himself as a mermaid with a bowl of fruit just to tease the marooned and starving Felix. He quickly sheds the disguise and sicks a shark after Felix.

HIM, the Flaming Devil from The Powerpuff Girls, usually dresses in a fuzzy pink skirt and thigh-high stilleto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.

Ice Man, of all characters, has a go at this in the beginning of the Mega Man episode "Ice Age".

In The Fairly Oddparents, Timmy managed to humiliate Crocker on a global scale and get him arrested for developing a supposed computer virus by uploading a video file of himself modeling one of his mother's dresses.

In The Simpsons, episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be a genuine Transsexual so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)

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